As for Shep... He was probably the most one-dimensional top six forward the Wings have had in the last 15 years. He had a great shot and nothing else. His skating ability probably rivals some of the NHL's worst. He had almost no playmaking ability. He was irrelevant defensively. He was not gritty or physical at all. He didn't bring any intangibles. Oh, yeah, but he scored 50 goals in a high scoring era with one of either of two amazing set up men at his side (either Feds or Yzerman, depending on which season). Was he instrumental in winning a cup? Hell, no.
As for Vladdy... I love the guy. Maybe he gets a sentimental (but perhaps undeserved) #10 for what might have been, but there were others who played more and were at least equally instrumental in the Wings' success. If he had played on more than one cup team, then you have an argument. I have a hard time, however, ranking him above guys that were good players for more seasons and were in key roles on multiple cup teams.
You just described Luc Robitaille